American Revolution & Colonial Life Programs Pre and Post Lesson Plans & Activities The Culper Spy Ring One of the most successful spy operations on either side of the war was the Culper Spy Ring. The Spy Ring was created by George Washington to obtain intelligence about the British. Benjamin Tallmadge was key in creating the spy ring. Tallmadge became General George Washington’s chief intelligence officer, rising the rank of Colonel. The "Culper" name was suggested by Washington, inspired by Culpeper County, Virginia. Tallmadge identified childhood friends from Setauket. Many of them lived within a mile of each other and grew up together. He recruited them to take part in the spy ring, including Caleb Brewster, Abraham Woodhull, Austin Roe, and Nancy Strong. Caleb Brewster was an experienced sailor who could expertly navigate a whaleboat across Long Island Sound, an 18 mile journey. He knew all of the coves and shoreline of Setauket in Long Island. Privateers were akin to pirates, but were sanctioned by Connecticut. They were constantly making raids, spying and capturing enemy ships on Long Island Sound – this is why the Sound was called The Devil’s Belt. Patriots attacked, captured and sabotaged British ships – and vice versa. Privateers who were Loyalists from Long Island would come to Connecticut and kidnap people to hand over to the British - officers were highly valuable. Members gathered information about British forces headquartered in New York City and passed it on to Washington at his headquarters. To ensure their safety, they used elaborate codes, invisible ink, and fake names. Although the British knew that there was information being passed through Long Island, no one in the Culper Spy Ring was ever arrested. Robert Townsend (AKA Culper Jr.), was a New York City merchant. He collects information about the British in New York and passes messages to… Austin Roe, a tavern operator on Long island, who comes to New York City to purchase goods from Townsend, and receives messages stuffed in with his purchases. When he returns to Long Island, he buries the secret messages in a box on the farm of … Abraham Woodhull (AKA Culper Sr), who decides which ones to send on to General Washington. He uses a telescope to look at the clothesline hung by his neighbor… Anna Strong. If she hangs a red petticoat and a series of white handkerchiefs, it signals that… Caleb Brewster, who commands a fleet of whale boats in the Sound, has arrived and is waiting in one of the local coves. He carries the message to Fairfield, where he passes it on to another messenger until it gets to Washington’s headquarters. At the Fairfield Museum: • Students will view items owned by Caleb Brewster, a sailor from Setauket. • Students will see the grave marker for Caleb Brewster. Fairfield Museum & History Center | Fairfieldhistory.org | American Revolution: The Culper Spy Ring Fairfield Museum & History Center | Fairfieldhistory.org | American Revolution: The Culper Spy Ring A drawing by William Lee (former Fairfield Town Historian) depicting a whaleboat like the type used by Caleb Brewster and privateers, used with his permission . Fairfield Museum & History Center | Fairfieldhistory.org | American Revolution: The Culper Spy Ring Additional Resources Online: Start here to read a brief history about the Culper Spy Ring https://connecticuthistory.org/caleb-brewster-and-the-culper-spy-ring/ Culper Spy Ring https://www.history.com/topics/american-revolution/culper-spy-ring Culper Spy Code Activity: http://teachitct.org/grade-5-caleb-brewster-the-culper-ring/ Turn to a Historian "TURN to a Historian" is an independent blog for people searching for historically-accurate information and analysis about "TURN: Washington's Spies", AMC's fictionalized television drama about Revolutionary War spies. Written and compiled by Rachel Smith, who works for the Office of the Connecticut State Historian at the University of Connecticut, as a historical consultant, and as an administrative editor for Common-place, an online academic journal of Early American History. https://spycurious.wordpress.com/ Van Locke Murals in Setauket, Long Island Scroll down on this page to view depictions of the spy ring in murals at Setauket School, Long Island. http://www.threevillagehistoricalsociety.org/?page_id=4583 Spy Letters of the American Revolution: From the Collections of the Clements Library A fascinating website full of primary sources, including • Gallery of Letters • Stories of Spies and Letters • Secret Methods • People of the Revolution • Routes of the Letters • Timeline • Sir Henry Clinton Collection • Teachers’ Lounge • Make Invisible Ink: http://clements.umich.edu/exhibits/online/spies/lounge-activities.html Fairfield Museum & History Center | Fairfieldhistory.org | American Revolution: The Culper Spy Ring Caleb Brewster was born in Setauket (near present-day Port Jefferson), Long Island, in 1747. He was the son of Benjamin Brewster, grandson of Daniel Brewster, and great-grandson of the Rev. Nathaniel Brewster (the first minister of the old town church in Setauket) who is supposed to have been a nephew of Elder William Brewster, who arrived with the pilgrims. Caleb was an active boy and was anxious to explore the world beyond his native village, so at the age of 19 went on a whaling ship bound for the coast of Greenland. On return from London in a merchant ship, he arrived to find the country engaged in the Revolutionary War. He immediately volunteered and soon was made a lieutenant of artillery. He was held in high esteem by his officers and the commander in chief for his integrity, courage and patriotism and became an important member of the Culper Spy Ring. Under the direction of Major Benjamin Tallmadge, Brewster provided important information relative to the movements of the British Army in New York and on Long Island. Brewster was among those who under Col. Parsons crossed the sound in 1777 for the purpose of capturing a company of British soldiers who had taken possession and made a fort of the Presbyterian Church at Setauket. This expedition was not successful, as, while they were making their attack on the British in the old church word came that reinforcements were coming down the sound to the aid of the British, so the attack was abandoned. For several years, Brewster was the trusted messenger of the secret messages from Setauket to the headquarters of major Tallmadge, across the sound, and in his lightly armed whaleboats, with good men, traveled this route as often as was necessary. he sailed under his own name and made no attempt to keep secret which side he served on. In addition to this he captured several supply ships headed for the British Army in New York, and also led his men on raids across Long Island, burning and wrecking whatever they could find belonging to the British. He had many encounters with the enemy and was sometimes wounded, but always came off victorious and was never caught. Austin Roe of Setauket, brought the secret messages from the chief spy in New York, Robert Townsend (alias Culper, Jr.). These were turned over to Abraham Woodhull, who in turn gave them to Caleb Brewster, who carried them across the sound in one of his boats and delivered them to Major Benjamin Tallmadge, who delivered them to General Washington, wherever he might be located. He was with Major Tallmadge in November 1780 in the expedition that came across the sound from Fairfield, Conn., and landed at Mt. Sinai; then marched across the Island and made a successful attack on the British Fort St. George at Mastic. They returned the same way with their prisoners and part of the force went back by the way of Coram, where they burned a hay stack of 300 tons collected by the British. On December 7, 1782, Capt. Brewster, with the whaleboats under his command, gave chase to several armed boats of the enemy in the sound, and after a desperate fight succeeded in capturing two of them. During this encounter his shoulder was pierced with a rifle ball and he was hospitalized for some time, after which he was placed on the pension roll of the army for the rest of his life. He was engaged in several other important encounters with the enemy on the water after this, and in 1783 captured the Fox, an armed British vessel in the sound during a short but fierce encounter. In 1784 he married Anne, daughter of Jonathan Lewis of Fairfield, Conn., where he continued to live when not in public service. He was long remembered for his great size, his fine proportions, vigorous constitution, unrivaled wit and his devil-may-care bearing. He died on his farm at Black Rock, Conn., at the age of 79. http://www.longislandgenealogy.com/patriots.html#brewster Fairfield Museum & History Center | Fairfieldhistory.org | American Revolution: The Culper Spy Ring .